Stein Overtoom

Co-founder & CEO, Lassie · 1 appearance on the record.

computed by AI from the episodes · how this works → · full disclaimer →

founderexecutiveoperator@steijnpelle ↗steijn.com ↗

He is the co-founder and CEO of Lassie, an AI startup that automates administrative tasks and workflows for dental practices and small businesses. Prior to building Lassie, he worked as an early product manager at Robinhood, Coinbase, and HealthTap.

9statements → 6claims → 2claims resolved → 3.78/5average certainty → 1.89/5average debate potential →

1 supported 1 partly supported 0 contradicted 4 not checkable as stated how the 6 claims stand · each chip opens the sources

6 assertions · 2 insights · 1 disclosure · every statement was checked. The predictions and assertions are the 6 claims: statements the public record can support or contradict. 2 are resolved, and 4 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Stein argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported

Overtoom: US dental practices each spend roughly $200,000 annually on administration

“There are about like, 160,000 dental practices in the U.S. Alone. And like, they spend roughly 200,000 dollars a year on like, administrative costs.”

Stein Overtoom Jul 29, 2026 ▶ 14:54 “Every small business should run itself” | Lassie with a16z

How they sound: speaking style how? →

300 words/min while actually speaking · 47.1 um and uh per 1k words

No argument clarity score for Stein Overtoom: no usable question→answer exchanges on raw tape (a fair score needs 8+). We do not score a sample that small. Roundtable and news formats yield far fewer direct exchanges than interviews.

Measured by listening to the audio itself: 5,781 words across 1 episode of raw-level tape, transcribed verbatim with every um and uh kept, each one attributed only where the alignment onto our timed stream is unambiguous. These are measurements of speaking style. We do not rank them: across this corpus, fluency and argument quality are nearly uncorrelated (ρ≈0.2), and smooth talking does not signal clear thinking. How it's measured →

What they said9 Episodes1

Everything Stein Overtoom said on the a16z Podcast that made the record, most notable first. Filter by type, assessment or year in the ledger →

Disclosure

Overtoom: Lassie charges five figures for an agent doing 30 hours monthly

“We are already charging five figures for kind of like this first agent that only does 30 hours of labor a month.”

Stein Overtoom Jul 29, 2026 ▶ 16:17 “Every small business should run itself” | Lassie with a16z

Assertion Not checkable as stated

Overtoom: Lassie's first agent achieves a 98% automation rate

“For the first agent, 98% of the work and then there's a sliver left. And then the interesting thing that we have thousands of staffers that are basically giving us input. On how to make that appeal that the agent currently cannot do.”

Stein Overtoom Jul 29, 2026 ▶ 21:37 “Every small business should run itself” | Lassie with a16z

Assertion Not checkable as stated

Overtoom: Demand for dentists and plumbers is double current supply capacity

“If you just look at the dental practice, but the same applies to try to find a good plumber there's just like twice as much demand that currently can be supplied.”

Stein Overtoom Jul 29, 2026 ▶ 43:33 “Every small business should run itself” | Lassie with a16z

Assertion Not checkable as stated

Overtoom: Hundreds of thousands of small practices handle billing manually

“There are, like, hundreds of thousands of these small businesses that literally, like, do this all by hand.”

Stein Overtoom Jul 29, 2026 ▶ 3:32 “Every small business should run itself” | Lassie with a16z

Assertion Not checkable as stated

Overtoom: US dental automation is a $1B recurring revenue market

“Serving that market first, you're looking at a one billion dollars in like a recurring revenue as a market.”

Stein Overtoom Jul 29, 2026 ▶ 34:40 “Every small business should run itself” | Lassie with a16z

Insight

Overtoom: All small businesses share the exact same core administrative workflows

“All small businesses at an abstract level, Like have a system of record they need to read and write into. They all have customers in doctor offices. They happen to be patients, but it's interacting and transacting around payments. You need to book appointments…”

Stein Overtoom Jul 29, 2026 ▶ 35:10 “Every small business should run itself” | Lassie with a16z

Insight

Overtoom: Standard B2B databases like Apollo and LinkedIn fail for SMB sales

“Because if you were to sell to like me, you like find me, you know, in clay and you enrich it with some Apollo data, and then you look me up on LinkedIn, then you know, again, this is the guy that's going to buy my HR system. We can't really do that because Dr…”

Stein Overtoom Jul 29, 2026 ▶ 57:14 “Every small business should run itself” | Lassie with a16z

Assertion Supported

Overtoom: US dental practices each spend roughly $200,000 annually on administration

“There are about like, 160,000 dental practices in the U.S. Alone. And like, they spend roughly 200,000 dollars a year on like, administrative costs.”

Stein Overtoom Jul 29, 2026 ▶ 14:54 “Every small business should run itself” | Lassie with a16z

Assertion Partly supported

Overtoom: 70% of small US healthcare practices are still paid on paper

“I think the stats are 70% are still paid on paper. And it's going through this massive, like, digitization revolution right now, because federal inflection point, that's regulatory.”

Stein Overtoom Jul 29, 2026 ▶ 53:54 “Every small business should run itself” | Lassie with a16z

Appearances (1)

Episode	Date	Speaking time
“Every small business should run itself” \| Lassie with a16z	Jul 29, 2026	24m

Stein Overtoom

The record, in short

Their most notable supported claim

How they sound: speaking style how? →

Appearances (1)

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